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Adult Confessions | Embarrassing-moments |
Embarrassing Moments
We've all had them - those truly hateful embarrassing moments, caught with your finger up your nose, or snooping through a medicine cabinet, sneezing snot all over a fellow passenger, or realizing you forgot to set the parking brake after your car rolls into a gully, or needing to wrap your jacket around your waist when your period unexpectedly started when you were wearing white pants.

This section of AdultConfessions.com is here just to chronicle those most embarrassing moments. Let the whole world know your bad habits, and when you got caught committing them.
  • — Embarrassing Moments —
    Straight Male / 26

    Came home yesterday for Memorial Day weekend to visit my mom. No biggie right, just seeing family. I never pack cloths because I have a bunch at home still so my mom just gives them a fresh wash prior to me coming.

    I always forget she has me stocked up on tighty whities but since itâs just weekend or sometimes a single week visit I just wear them. Isnât like no one else is gonna see them. Of course my mom has opinions on underwear and sheâs always preferred briefs.

    Well where this gets embarrassing is I was on this website last night after I showered, sitting at the desk in my room in my tighty whities hard as ever! I was leaned back in my chair, pulled my hard on and balls out the fly to masturbate.

    And my mom walks in. All she said was put your penis back in your briefs,your not a teen anymore you donât need to masturbate every chance you get! Meanwhile Iâm standing there hard sticking out of my briefs an I told her it has to go flaccid before a guy can get it back though the fly! So she said well hurry up and ave an orgasm, clean up and get dressed so we can go to the store.

    After she left I had a big orgasm. That is the first time I had gotten caught since I was 14. When I came out all dressed she asked if I got everything out of my system. Way embarrassing questioning! She asked if my briefs fitted fine still and if I changed them afte masturbating. I told her they fit as briefs should and no I didnât get anything on them so why change them.

    #40309 — Comments (1) — May 26, 2018 at 12:20 PM — That's Juicy! (7) Remove This.
  • — Embarrassing Moments —
    Straight Male / 39

    I'm so excited again. It's Saturday morning and as I do every Saturday, it's my day to go serve a couple of young girls. By serve them I mean they call me their maid. I do all of their laundry and cleaning. Go buy them makeup or whatever else they send me for. In exchange, they usually make me wear their underwear or keep me naked. They often have other girls that come over and tease me about wearing panties. If other girls see me naked, I have to give them money so they have no problem making me undress for their friends.

    #40308 — Comments (1) — May 26, 2018 at 8:46 AM — That's Juicy! (4) Remove This.
  • — Embarrassing Moments —
    Transsexual Female / 50

    I started at the age of 8, wearing my motherâs panties, bras, stockings, shoes, dresses and night gowns. By the time I was 11 I was dressing completely wearing my moms wigs, wearing makeup, and walking around dressed like her. I was her height and her clothes fit just right. There was no sexual pleasure per say. I hadn't started to get pleasure from masturbation yet. The feel of the clothes was something I really enjoyed, seeing myself as a female felt normal. The first time I actually got off wearing her clothes was when I was 12. I was dressed up, the feeling was stronger then ever, when I felt this sensation coming from deep in my balls, then I shot my load to my surprise in the panties. After that the sexual side kicked in big time. Every chance I had I would wear women's clothes. By now any women's clothes got my attention and attraction. I would take clothes off the clothes line in backyards at night. I got to experience all kinds of clothes. If visiting some one I would find a way to nose around. And if the opportunity came up, I would try on their clothes. More then once my mother found her items moved or a stain in them but she never approached me about them directly. I remember once she found a long shinny silk night gown in my room. She just took it back. I never got caught until I was 14. I had one of motherâs wigs and basic makeup with me. There was a house 2 blocks down from ours where this 50ish woman lived alone. I would cut her grass every 2 weeks. I knew her yard real well so I could walk into it at night. She always left her shoes outside the back door. She didnât wear shoes in her house. So I could count on finding something there always. I had grabbed a dress, panties, and bra from another yard off the clothes line. I used the extra panties to stuff the bra. Then went and got some shoes, I found some flat sandals. Wearing the wig & some makeup I went out walking around dressed up. It was about 2am, I had walked about 10 blocks from the house. Hadn't seen anyone since it was a weeknight. A car passed me, and kept going. I turned on to a side street to head back, when the car pulled next to me, the man offered me a ride. I just kept walking; he pulled ahead of me, and then got out. He walked up and grabbed my arm. He said youâre a cutie baby. He tried to kiss me on the mouth. I resisted, but he was bigger then me by at least 10 inches, and 100lbs. As he manhandles me, he pushed me down on the grass in front of this house. He then said baby I want you. He opens his pants and flipped out his dick, it was good and hard, I froze. He got on top of me trying to get between my legs, I was able to roll over, and get on my stomach, but that only worked to his advantage, he pinned me down with his arm, and then pulled up the dress I was wearing to my waist, I was wearing only panties. He pulled the panties down exposing my cheeks. He said you are nice, love that ass. Then I felt his dick in my cheeks, he pushed in but nowhere to go, he then spread open my cheeks, drove it home into my ass, I cried out, but he had me. He proceed to pump, as he did he kissed my neck, he reached around and grabbed my boobs, which were panty specials that I had gotten off the clothes line, he smelled of cigarette and booze. After about what seemed forever he finally shot his load into me. I could feel every squirt as it went into me. I had tears running down my face, the little makeup I wore was smeared, and here I was full of a man's dick in my ass. He got out of me and rolled off to one side. I looked over at him and he just smiles back at me. I laid there not knowing what to do. He got up, told me I was really a good piece of ass.
    As I rolled over to get up, he stood in front of me, and then told me to clean him up, I wasn't sure what he wanted, he slapped me hard, and said clean my cock bitch. He reached down and grabbed my hair, when he yanked, the wig came off, and he said what the hell!
    He grabbed the bottom of the dress and pulled it up high exposing me, what the hell are you, I didn't answer. Well what ever you are suck my cock now. With that he pushed his dick into my mouth; I choked as he pushed in deep.
    The taste was awful to me, but soon it got worst. He said now take this, and he let loose again filling my mouth with his cum. I swallowed some and the rest came out on my face and landed on the dress. Once he was done he pushed me down on the grass again, he zippered himself up and walk to his car and drove off leaving me there. I must have laid there 30 minutes before I got up and dressed myself again, replaced the wig and went towards home. I replaced the shoes, then went by the house where the clothes came from and return them to the clothes line, then went on home. I felt sick for about a week after that thinking what he had done to me. I was ashamed but couldnât tell anyone about it. It was about a month later that I told my aunt everything, including that I had worn her clothes. She listened and then hugged me. She advised me to let it go, and be careful, and not get runs in her stockings. Well i kept dressing up when I turned 16 I wanted more. I sneaked out around midnight and had my mother's wig and high heels. I grabbed panties and a bra and pantyhose off a clothesline like I had done so many times before. But this time I walked about a mile to a major street. I could walk like a woman moving my hips. A few cars went by it was around 2 am not many cars out. Finally after about 30 minutes this car pulled up. this older guy driving. he asked if I needed a ride? I said i could give him a ride. He said 10 for head I said sure. I climbed in he parked on a side street. I got busy. It didn't take long for him to reward me a nice mouthful. Once done I got out and waited for another car to pulled over. it was about 3 am by now and another man pulled up. made the same offer he said get in. he parked along the side street, he told me to get in the backseat, once he joined me he undid his pants and told me to get on my knees, he lifted the dress and pulled down my pantyhose and panties, in the darkness he couldn't see my dick, he grabbed my hips and got behind me moving his cock to find my hole, he found it and shoved it in hard, but in it went. It was feeling good and he said I am cumming just then a tap on the window. A city of Miami Police officer. The guy pulled out of me, and fixed himself, I pulled up my panties and pantyhose then fixed my dress. He said get out, he asked for ID. The guy showed his D.L I said don't have any. he told the guy to get lost which he did fast. the cop told me to come with him. He had me lean onto the trunk of his squad car he frisk me. He found the $30 I had in my bra. He told to me bring my hands back and he cuffed me saying I was being arrested for prostitution. He drove to the local office. he took me in and sat me a desk. Another cop came over and asked me a bunch of questions. That is when they figured out my age and sex. The second one grabbed my arm and took me home in cuffs. he knocked on the door, my mother answered, she was like what is going on. the cop explained where I was picked up and what I was doing. And how much money I had in my bra. She was flipping out. the cop left me with her. My dad wasn't home he was at a convention in Tampa. She dragged me to her bedroom and started yelling at me. Whose clothes I was wearing, those are my shoes and wig. So I told her about the clothesline. Then she wanted to know what i did for the money. She was crying you're a cheap whore. she lifted the dress and looked underneath. She saw the wet stain in the panties. She yanked the pantyhose down and then the panties followed. She stuck her hands between my cheeks, her fingers came up and she smelled them. This is a man's sperm. She said go to bed we will talk in the morning. i could have died right then. But morning awaited me. In the morning I was so embarrassed and shameful. When got up she asked me you want to be with men? You want to be a woman? Then she asked how many men have used me? I told her everything. She said no more whoring. She never said another word about it.

    #40237 — Comments (1) — May 18, 2018 at 2:32 PM — That's Juicy! (4) Remove This.
  • — Embarrassing Moments —
    Bi-Sexual Male / 55

    I was visiting friends on my way to Florida and they invited me to use the guest room instead of a hotel. I welcomed the idea and said goodnight. We planned to meet for breakfast. I think I was asleep before my head hit the pillow. A few hours later I was awakened by soft lips kissing my hardening cock. The room was pitch black and I made no effort to know who was sucking my cock. I thought it might be Kim, Tom's wife, but I wasn't sure. It was a sensational blowjob and soon I came in what I thought was Kim's throat. Whoever it was quickly left and I was soon back asleep. That morning at breakfast Kim acted quite normal and it was then I noticed their daughter Katie sitting at the table eating some yogurt.
    She grinned at me and while he parents weren't looking she open her mouth full of yogurt and gulped it down. My head felt like it was going to explode. Katie is only twelve years old. I feel sick to my stomach. I know in my heart I would never have allowed it to happen if I had my wits about me. Tom and Kim left for work and I was home alone with Katie. She came on to me but I made it very clear that nothing else was going to happen. But she was a persistent little slut so I let her blow me again and she begged me to fuck her. I ate her sweet little pussy and she came hard three times. I rubbed my hard cock on her pussy and and shot my load on her tummy. I feel terrible about what happened.

    #40202 — Comments (1) — May 15, 2018 at 9:40 PM — That's Juicy! (9) Remove This.
  • — Embarrassing Moments —
    Bi-Sexual Male / 25

    Most of the people that know me call me Barry Blowjob. That is because my name is Barry and I have my lips wrapped around other guyâs cocks almost constantly. I love sucking cocks so much. I love the feel of a big cock sliding deep into my throat. I also love the yummy taste of cum. Itâs embarrassing but I canât stop it.

    #40191 — Comments (8) — May 14, 2018 at 3:29 PM — That's Juicy! (4) Remove This.
  • — Embarrassing Moments —
    Straight Female / 19

    My brother's best friend has become part of our family. I think he espends more time at our house than he does in his own home. I was showering in the up stairs bathroom like I do every day, but that day would turn out to be an embarrassment. I don't know why my brother's friend decided to use the up stairs bathroom on day I had forgotten to lock the door. There's a bathroom down stairs he could bad used. Till this day I can't figure out if my brother told him to used the up stairs one because he was going to the one down stairs, or intetionally picked the lock to play a prank on me. I always lock it but maybe I just forgot. Any way, I was stepping out of the shower when the door flew open and there was his friend saying "oh shit I'm sorry" giving me all sorts of excuses, looking me over and taking his sweat time doing it. Never felt so naked and embarrassed in my life. He finally closed the door and stood there thinking "oh well these things are bound to happen" Going down stairs and facing him proofed to be my second embarrassment. Had he told my brother? Had my brother and him planned the whole thing? Had I really forgotten to lock the door? The reality was that I had gotten caught bare ass naked and nothing was going to change it. For days he kept coming to our house acting like it never happed. One day he told me to not worry because he would never tell anyone. I'll never forget his answer when I asked him how much he saw. He said "everything" with a smile on his face.

    #40178 — Comments (1) — May 13, 2018 at 4:35 PM — That's Juicy! (4) Remove This.
  • — Embarrassing Moments —
    Straight Female / 47

    i play with my tits and pussy all day everyday for the past 30 years and so ugly can't get a man. fuck you world. you gone and cop a punching face full soon. very soon! for this.

    #40167 — Comments (4) — May 12, 2018 at 2:52 AM — That's Juicy! (6) Remove This.
  • — Embarrassing Moments —
    Straight Male / 46

    A few years back, my mother in-law was visiting us like she did 4 times a year. One night I had to work late, by the time I walked in everyone was laying down. My MIL slept in the guest bedroom on the other side of the house. She was deep sleeper and she wore hearing aids which she took out at night. My wife was feeling risky when i walked in. Needless to say i wasn't going to turn her down. my wife over the years had developed a love of me licking her ass. During our session I was working her ass hard with my tongue, she started up saying loudly yes eat my ass, stick that tongue into my ass, fuck my ass with your hot tongue. You like my taste don't you, suck my ass. At some point she called out now fuck my ass with your cock i want to feel you cum in my ass. We ended our night a while later. In the morning I got up and headed off first to my office having an early meeting at 8:30 am. My wife must have followed a few minutes later to have her coffee. It was during that time her mother came out and asked her about what kind of woman she was? My wife asked why? She plainly told her I was up last night with indigestion I was sitting on the sofa, and I heard you calling out to have your ass eaten, and how you wanted to feel his tongue in your ass, then you wanted him to fuck your ass. My told me she dropped the cup. Her mother just stood there looking at her. My felt like a little girl who was caught being bad. Her told her she didn't raise her to a slut. She told her mother that she enjoys our sex life and left for work. She emailed me and said to call er at lunch time. Which I did. She informed what had occurred. We agreed to say nothing more to her about it. By the time I got home they had talked some more and she going home early. I played dum. She went home. It was about 5 years later I had to go and over see the replacement of my MIL water heater. While I was there after the work was done she took a hot bath. When she came out she was wearing a wrap around towel. walking back to her bedroom past the kitchen where I was sitting. It was barely covering her cheeks. i could see a lot more than I wanted. She stopped at her doorway and she asked me "want to lick my ass"? Then she dropped her towel. She actually had a nice ass, and very nice hairy bush, plus those large breasts. I got up and went in behind her. Within the hour she was saying the same things my wife had. It was fun and lasted only a few months after that. She would go on and suffer a heart attack. I guess like daughter like mother. And yes I did admit it all to my wife when I got back. she mad at first but then figured her mother needed some pleasure after years of nothing.

    #40144 — Comments (0) — May 9, 2018 at 12:29 PM — That's Juicy! (2) Remove This.
  • — Embarrassing Moments —
    Straight Female / 47

    i prank called a company that ripped me off and wrote to a hooker store for some sex toys from one the managers just to piss them off. I hope they get got the dick up the ass !

    #40102 — Comments (0) — May 4, 2018 at 10:41 PM — That's Juicy! (1) Remove This.
  • — Embarrassing Moments —
    Transsexual Female / 24

    Jail bait
    19, female. From ages (14-17) I used to talk to older guys, sometimes as old as 45. I had naturally big breasts for my age and I would talk sexually and exchange pictures or videos (nude). Iâve done this hundreds of times (not meeting in person) although I wanted too. And Iâve finally realized how wrong it was at the time that I was basically talking to *p**ophiles* but I liked it..CARLSS

    #40029 — Comments (1) — Apr 20, 2018 at 11:12 PM — That's Juicy! (2) Remove This.
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